Reaction #10188

Reaction equation

methanol CH2Cl2

HOAc

ethoxymethylenemalononitrile

4-Butylamino-5-amino-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-10-carboxylic acid tert-butyl ester

→

7-Butyl-5,7,13-triazatetracyclo[9.3.1.02,10.04,8]pentadeca-2(10),3,5,8-tetraene-13-carboxylic acid tert-butyl ester

Solvents

ethanol

Conditions

Workup

1. 1
   TemperatureThe reaction was cooled
2. 2
   Concentrationconcentrated
3. 3
   workup.ADDITIONtreated with H2O and saturated aqueous Na2CO3 solution
4. 4
   Extractionthen extracted with ethyl acetate (3×50 mL)
5. 5
   Dryingdried (Na2SO4)
6. 6
   FiltrationAfter filtration and concentration
7. 7
   Otherthe residue was chromatographed
8. 8
   Otherto provide a yellow oil

Procedure

4-Butylamino-5-amino-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-10-carboxylic acid tert-butyl ester (440 mg, 1.27 mmol) was dissolved in ethanol (20 mL) and HOAc (2 mL) and treated with ethoxymethylenemalononitrile (186 mg, 1.52 mmol). The resulting mixture was warmed to 60° C. and stirred 18 hours. The reaction was cooled, concentrated, treated with H2O and saturated aqueous Na2CO3 solution then extracted with ethyl acetate (3×50 mL) and dried (Na2SO4). After filtration and concentration, the residue was chromatographed to provide a yellow oil. (400 mg, 89%). (TLC 5% methanol/CH2Cl2 (NH3) Rf 0.70).

Source